Roadtripping Thru Grief

In 1988, the movie Cocktail came out.  I loved it, I still love it.  I was 14 years old when it was released. 

From the first time I watched it, I remember saying to myself and others, “One day I’m gonna move to the Caribbean and open a Tiki Bar.”  When one of the VHS rental stores was going out of business, my mom bought me a copy of the movie.  When I digitized the VHS home movies, I included Cocktail as well.

The Caribbean lifestyle has drawn me in since before I ever visited in person. It definitely caught my attention when I watched that movie. The palm trees, the salt water, the sound of the waves, the music, the slow pace…all of it was a dream. I’ve been very fortunate to travel. I’ve been to beaches in almost every coastal state, including those around the Great Lakes. I’ve been to beaches in Hawaii, Mexico, England, and the Florida Keys. In 2002, I traveled to the Caribbean for the first time, St. Croix. In 2014, I spent my 40th birthday in Grand Cayman.  Both islands were beautiful but didn’t quite seem doable or like “the” spot.

In 2024, I took a cruise for my 50th birthday. One of the ports of call was San Juan, Puerto Rico.  At the last minute, I booked an excursion to walk around Old San Juan.  As soon as I stepped off the ship, it felt doable and peaceful.  I can’t explain the feeling that came over me.  I knew nothing about the rest of the island. However, I almost immediately booked a trip back to check out the whole island. 

Puerto Rico has it all, in my opinion. Beaches and mountains, city and country, convenience shopping and side of the road markets, award winning restaurants and food trucks, Spanish and English (I’ve even used my sign language skills quite a bit). If it doesn’t have it all, the rest of the islands are a short ferry ride or cheap plane ride away.  I plan to explore as many islands as possible.  Maybe this island isn’t forever, but I’m loving it so far.

Within 6 weeks of being on an island for about 5 hours, in only a small area, I was looking for a place to live and what type of work I could do on the island.

Family, friends, coworkers, and strangers ask me,  “Why Puerto Rico?!”  It’s not an easy answer.  From the outside looking in, it seems kind of crazy, quick, and impossible.  Throughout life, there are windows of opportunity, and if you don’t jump out the window at the right time, it may never open again.  I found the place, I just needed to get everything else to fall in line.

“One day I’m going to move to a Caribbean island and open a Tiki Bar”.  37 years later, lots of life, careers, moves, and death in between….I’m half way there.  I’ve had other dreams, however, I remember exactly when this dream started and it has stayed with me as other dreams have come and gone.